Potassium Cyanide → 3-Pyridineacetonitrile, 6-(trifluoromethyl)-

HRID 512136

Reaction equation

HRID 512136 reaction equation
Cl[CH2:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([F:12])([F:11])[F:10])=[N:7][CH:8]=1.[C-:13]#[N:14].[K+]>C(O)C.O>[F:10][C:9]([F:12])([F:11])[C:6]1[N:7]=[CH:8][C:3]([CH2:2][C:13]#[N:14])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 9032Potassium CyanideHCID 27738105-(Chloromethyl)-2-(trifluoromethyl)pyridine

Product 1

HCID 508511273-Pyridineacetonitrile, 6-(trifluoromethyl)-Yield 75%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

5-Chloromethyl-2-trifluoromethylpyridine (19.5 g, 99.7 mmol) in ethanol (160 mL) was added to a solution of potassium cyanide (9.74 g, 150 mmol) in water (80 mL) at 90° C. over 30 minutes. The mixture was stirred at 90° C. for 3 hours. Most of the ethanol was removed under reduced pressure and the aqueous layer was extracted with AcOEt (3×100 mL). The combined organic extracts were washed with water, brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel chromatography (30% AcOEt in hexanes) to afford (6-trifluoromethylpyridin-3-yl)-acetonitrile as a brown oil (9.79 g, 75%). 1H NMR (400 MHz, CDCl3) δ ppm 8.63 (s, 1 H), 7.90 (d, J=8.0 Hz, 1 H), 7.70 (d, J=8.0 Hz 1 H), 3.88 (s, 2 H). 19F NMR (400 MHz, CDCl3):168 cm−1. MS m/z 187.14

Workup

  1. customMost of the ethanol was removed under reduced pressure
  2. extractionthe aqueous layer was extracted with AcOEt (3×100 mL)
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography (30% AcOEt in hexanes)

Sources & evidence

ORD record
ord-7072f7350d2b4bf6a701e027131eb1e4
Source dataset
uspto-grants-2015_08
Patent number
US09102591B2

Linked notes

Loading…